Arsenophenol.



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rAUL suction AND ALFRED BERTHEIM, or FRANKFORT-ON-THE-MAIN, GERMANY, ASSIGNORS T0 rannwnnns VORM. MEISTER Lucius & BRUNING, or noousr-ou- THE-MAIN, GERMANY,

A. CORPORATlON OF GERMANY.

AESENOPHENOL.

Ne. eoe,sso.

Patented Jan. 12, 1909.

Application filed Kay 1, 1908. Serial No. @80389.

' specification.

We have found that the hitherto unknown arsenoohenols, the constitution of which corresponds to the formula:

and which can be prepared by reducing the hydroxyarylarsinic acids, are valuable for medical purposes.

The reaction which leads to the new compounds may be explained by the equation:

' sonias, are capable of curing them.

As already mentioned, the arsenophenols are obtained from hydroxyarylarsinic acids by reduction, 2'. c. by the action or strong reducing agents. The hydroxyarylarsinic acids are produced. fromthe corresponding aminoarylarsinic acids by means of the diam-compounds. By the action of weak reducing agents on the hydroxyarylarsinic acids, hydroxyarylarsenoxids are produced which; on being further reduced, are also transformed into the arsenophenols.

The preparation of the arsenophenols is carried out for instance in the following nanner: 217 parts by weight of para-a1ninohenylarsinic acid are dissolved in 18 times its quantity of water, 200 parts by weight of concentrated pure sulfuric ac d are added and diazotization 1s eliected by allowing to flow into the mixture a solution of 74 parts by Weight of sodium nitrite. The thusformed diam-solution is heated until no further nitrogen evolves. The sulfuric acid is then removed from the solution by precipitation with barium hydroxid and the residual liquid is filtered and evaporated in cacao. The sodium salt of the hydroxyphenylarsinic acid is thus obtained and can be produced in a pure state as a slightly yellowish substance by crystallizatior from dilute alcohol. An aqueous solution of 16 parts by weight of this sodium salt is added to a solution of parts by w'eight'of sodium hvdrosulfite free "from water of crystallization. which has been neutralized by addition of 25 parts by weight of crystallized magnesium chlorid and 20 parts by weight of 30% caustic soda lye and then filtered. This mixture is heated for about one hour on the water bath. The reddish-- brown precipitate of arsenophenol thus formed is filtered and washed with water. When dry, the arsenophenol is a reddishbrown powder, insoluble in water and benzene but soluble in alcohol and acetone. In caustic soda lye it dissolves readily with a yellow color and forms a sodium salt which is precipitated by alcohol from concentrated solution. This sodium arsenophenolate, a yellow powder, is readily soluble in water, more ditlicultly soluble in alcohol.

Very similar to the arsenophcnol are the homologous con'ipounds which can be prepared by a similar process from the anal0 gous hydroxyarylarsinic acids; as for instance hydroxytolylarsinic acid.

C l-LCH,,.OHAsO},H (CH :OH: As 1 :13:53); hydroxyxylylarsinic acid (I l-l (Cl-I OlLAsOJL (CH :CH OH :AsOJ-Lzl :4 :2 :5)

Having now described our invention. what we claim is: I

i 1. As new products, the arscnophenols, the constitution of which corresponds to the formula:

in caustic soda lye and then form yellow ice colored sodium salts which are readily solulole in ater but more difficultly soluble in alcohol.

2. Asa new product, the arsenophenol, the

constitution of which vcorresponds to the formula."

a I ecl(ilisl1-lorown'powder Whichis insoluble in Water and benzene but readily soluble in alcohol, acetone and ether, and which (lissolves in caustic soda. lye with ayellow color PAUL EHRLlCl-l. ALFRED BERTHEIM,

- Witnesses:

JEAN GRUND, CARL GRUND. 

